Showing metabocard for Normetanephrine (BMDB0000819)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:04 UTC
Update Date2020-05-21 16:28:47 UTC
BMDB IDBMDB0000819
Secondary Accession Numbers
  • BMDB00819
Metabolite Identification
Common NameNormetanephrine
DescriptionNormetanephrine, also known as normetanephrine, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Normetanephrine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Normetanephrine participates in a number of enzymatic reactions, within cattle. In particular, Normetanephrine can be converted into 3-methoxy-4-hydroxyphenylglycolaldehyde through the action of the enzyme amine oxidase [flavin-containing] a. In addition, Normetanephrine and pyrocatechol can be biosynthesized from norepinephrine and guaiacol through the action of the enzyme catechol O-methyltransferase. In cattle, normetanephrine is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+/-)-normetanephrineHMDB
(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanolHMDB
3-Methoxy-noradrenalineHMDB
3-O-Methyl-noradrenalineHMDB
4-(2-Amino-1-hydroxyethyl)-2-methoxyphenolHMDB
alpha-(Aminomethyl)-4-hydroxy-3-methoxy-benzenemethanolHMDB
DL-N-NormetanephrineHMDB
DL-NormetanephrineHMDB
L-NormetanephrineHMDB
m-O-MethylnorepinephrineHMDB
N111HMDB
NormetadrenalineHMDB
O-MethylnoradrenalineHMDB
3 MethoxynoradrenalineHMDB
3-MethoxynoradrenalineHMDB
Chemical FormulaC9H13NO3
Average Molecular Weight183.2044
Monoisotopic Molecular Weight183.089543287
IUPAC Name4-(2-amino-1-hydroxyethyl)-2-methoxyphenol
Traditional Name(+/-)-normetanephrine
CAS Registry Number97-31-4
SMILES
COC1=CC(=CC=C1O)C(O)CN
InChI Identifier
InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3
InChI KeyYNYAYWLBAHXHLL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Ether
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point204 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.71ALOGPS
logP-0.39ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.99ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.71 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.94 m³·mol⁻¹ChemAxon
Polarizability19.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Adrenal Gland
  • Adrenal Medulla
  • Brain
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal MedullaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000819
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022265
KNApSAcK IDC00037562
Chemspider ID1200
KEGG Compound IDC05589
BioCyc IDNot Available
BiGG ID46080
Wikipedia LinkNormetanephrine
METLIN ID66
PubChem Compound1237
PDB IDNot Available
ChEBI ID144308
References
Synthesis ReferenceSejbal, Jan; Krecek, Vaclav. Method of preparing normetanephrine. Czech. (1992), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in catechol O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:
COMT
Uniprot ID:
A7MBI7
Molecular weight:
30485.0
Reactions
Norepinephrine + Guaiacol → Normetanephrine + Pyrocatecholdetails
Enzyme Details
2. Amine oxidase [flavin-containing] A
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21398
Molecular weight:
59758.0
Reactions
Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails